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4-Day Chicago Adventure Itinerary
Last updated: 2024 Jun 14Welcome to the Windy City
Morning
Start your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). This iconic observation deck offers breathtaking views of the city and is a perfect introduction to Chicago's skyline.
Afternoon
Head over to Millennium Park for a leisurely stroll. Don't miss the famous Cloud Gate sculpture (The Bean). For lunch, enjoy some deep-dish pizza at Lou Malnati's Pizzeria.
Evening
In the evening, catch a live performance at House of Blues. For dinner, indulge in some delicious seafood at Joe's Seafood, Prime Steak & Stone Crab.
Bedtime
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4.27Skydeck Chicago at Willis Tower (Sears Tower)
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4.27
Skydeck Chicago at Willis Tower (Sears Tower)
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4.69Millennium Park
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4.69
Millennium Park
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5.00House of Blues
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5.00
House of Blues
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Exploring Downtown Chicago
Morning
Begin your day with a visit to Art Institute of Chicago, one of the oldest and largest art museums in the United States. Grab breakfast at a nearby cafe before heading in.
Afternoon
Take a walk along Chicago Riverwalk and enjoy lunch at The Purple Pig, known for its Mediterranean-inspired dishes.
Evening
Spend your evening exploring the vibrant nightlife of The Loop. Dine at Girl & The Goat, renowned for its innovative dishes.
Bedtime
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4.61Art Institute of Chicago
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4.61
Art Institute of Chicago
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4.72Chicago Riverwalk
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4.72
Chicago Riverwalk
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Cultural and Historical Gems
Morning
Visit the historic Field Museum in the morning. It's home to extensive exhibits on natural history. Have breakfast at one of the museum cafes.
Afternoon
Afterward, head over to Adler Planetarium for an afternoon exploring space and science. For lunch, try some classic American fare at Portillo's Hot Dogs.
Evening
In the evening, take in a show at the iconic Chicago Theatre. Enjoy dinner afterward at RPM Italian.
Bedtime
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4.56Field Museum
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4.56
Field Museum
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4.61Adler Planetarium
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4.61
Adler Planetarium
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4.71Chicago Theatre
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4.71
Chicago Theatre
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Architectural Wonders and Shopping
Morning
Start your day with an architectural tour of the city by visiting Marina City. Have breakfast nearby before you start.
Afternoon
Spend your afternoon shopping along The Magnificent Mile, where you'll find numerous high-end shops and boutiques. For lunch, head to Au Cheval for one of their famous burgers.
Evening
Conclude your day with dinner at Bavette's Bar & Boeuf, known for its steakhouse fare. Afterward, enjoy a nightcap at one of Chicago's stylish lounges.
Bedtime
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4.84Marina City
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4.84
Marina City
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4.65The Magnificent Mile
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4.65
The Magnificent Mile
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Final Day in Chicago
Morning
Begin your final day with a visit to Shedd Aquarium. This renowned aquarium houses a vast array of marine life and offers interactive exhibits. Grab breakfast at a nearby cafe before diving into the underwater world.
Afternoon
After the aquarium, head to Grant Park for a relaxing afternoon. Stroll through the park and enjoy its beautiful landscapes. For lunch, savor some mouth-watering BBQ at Smoque BBQ.
Evening
Conclude your Chicago adventure with an evening at Navy Pier. Enjoy the rides, shops, and stunning views of Lake Michigan. For dinner, treat yourself to an unforgettable meal at Alinea, one of Chicago's most acclaimed restaurants.
Bedtime
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4.75Shedd Aquarium
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4.75
Shedd Aquarium
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4.70Grant Park
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4.70
Grant Park
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4.48Navy Pier
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4.48
Navy Pier
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